Iodine → HCID 86594021, compound

HRID 896667Notes

Reaction equation

HRID 896667 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.II.C(N(CC)CC)C.[S:18](=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]12[S:18][CH:3]1[CH:4]1[S:8][CH:5]1[CH:6]=[CH:7]2

Participants

7

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 660494-BromothiophenolHCID 23665763Sodium Bisulfite

Product 1

HCID 86594021HCID 86594021, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromothiophenol (16 g, 85 mmol) in CH2Cl2 (85 mL) was added iodine (10.7 g, 42 mmol, in CH2Cl2) and triethylamine (11.8 mL, 85 mmol). After 3 h the resulting reaction mixture was diluted with a sodium bisulfite solution and ethyl acetate. The organic extracts were washed (1N NaOH, brine), dried (MgSO4), filtered and concentrated. The resulting residue was stirred vigorously in hexane/ether for 1 h then filtered to afford the 4-bromobenzene disulfide compound as a white powder.

Workup

  1. customAfter 3 h the resulting reaction mixture
  2. washThe organic extracts were washed (1N NaOH, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-37a34fc5a24949639b17444d77d51f39
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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